4-Vinylpyridine → Bis[2-(4-pyridyl)ethyl]amine

A mixture or 4-vinyl pyridine (10.0 g, 95.1 mmol) and ammonium chloride (5.1 g, 95.1 mmol) was heated to reflux in MeOH (90 ml) under argon for 27 h. The resulting precipitate was filtered and the filtrate was concentrated on rotavap. The resulting residue was dissolved in H2O (200 ml) and basified with 2N NaOH to pH 10.5 and extracted with CH2Cl2 (3×100 ml). The Combined organic extracts were dried (anhydrous MgSO4) and concentrated to a yellow oil which was purified by column chromatography on silica gel (10% MeOH/CH2Cl2) to yield the title compound (4.0 g, 18.5%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 8.50 (d, 4H), 7.10 (d, 4H), 2.93 (t, 4H), 2.80 (t, 4H), 1.81 (br. 1H); MS (ES) m/e 228.2 [M+H)+.

1. filtrationThe resulting precipitate was filtered
2. concentrationthe filtrate was concentrated on rotavap
3. dissolutionThe resulting residue was dissolved in H2O (200 ml)
4. extractionextracted with CH2Cl2 (3×100 ml)
5. dry with materialThe Combined organic extracts were dried (anhydrous MgSO4)
6. concentrationconcentrated to a yellow oil which
7. customwas purified by column chromatography on silica gel (10% MeOH/CH2Cl2)

ORD record

ord-b318ec746db043a4ba9d7711cc444d7c

Source dataset

uspto-grants-2000_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06037343